Riverside FL Multi Generational Style Homes for Sale

Welcome to 1521 Charon Road, ideally located in one of Jacksonville's most inviting and convenient neighborhoods. This property offers added privacy with no rear neighbors, creating a peaceful backyard setting perfect for relaxing, entertaining, or enjoying time with family and friends. A standout feature is the two-story accessory dwelling unit, complete with a loft-style bedroom upstairs. This versatile space offers excellent potential for guests, a home office, studio, rental income, or multigenerational living. Just a short walk from Fishweir Park, the home is situated in a friendly, established neighborhood with convenient access to the restaurants, shops, and local favorites of Murray Hill and the Shops of Avondale. Downtown Jacksonville is also only minutes away. With its combination of privacy, flexible living space, walkability, neighborhood charm, and central location, this property offers a unique opportunity to enjoy the best of Jacksonville living.

1521 Charon Road, Jacksonville

Listing courtesy of SERVICE REALTY, LLC.

$875,000

6 Beds ⋅ 4 Baths ⋅ 2145159 MLS

*Open House Sat, 5/23 & Sun 5/24 11A-1P* HISTORIC AVONDALE CHARM with over 4000 square feet meets modern functionality on an oversized 50' x 240' lot! This beautifully maintained property offers a rare combination of character, space, and flexibility with a 2829 square foot main house, DETACHED 4-CAR GARAGE and an 1178 square foot, FULL 2 BEDROOM APARTMENT perfect for guests, multigenerational living, rental income, or a home office setup. The main home welcomes you with a covered front porch and timeless historic details. The UPDATED KITCHEN features leathered granite countertops, farmhouse sink, built-in refrigerator, double drawer refrigerator, pot filler, and gas stove. MULTIPLE FLEX SPACES provide endless options for a home office, playroom, gym, or additional living areas. The living room is equipped with surround sound speakers, and the upstairs AC has been recently replaced. The DETACHED APARTMENT includes a kitchen, full bathroom, 2 bedrooms, great room, all-in-one washer/dryer, and abundant storage space. Step outside to enjoy the covered back patio, expansive green space between the home and garage, gated driveway and irrigation system. With ROOM FOR A POOL and an unbeatable Avondale location close to shopping, dining, parks, and the St. Johns River, this property is truly one-of-a-kind. Step outside to enjoy the covered back patio, expansive green space between the home and garage, gated driveway and irrigation system. With ROOM FOR A POOL and an unbeatable Avondale location close to shopping, dining, parks, and the St. Johns River, this property is truly one-of-a-kind.

1405 Challen Avenue, Jacksonville

Listing courtesy of KELLER WILLIAMS JACKSONVILLE.

Selling Office: .

$390,000

3 Beds ⋅ 3 Baths ⋅ 2140556 MLS

Located in the highly sought-after Avondale community, this charming single-family home offers a rare opportunity to enjoy one of Jacksonville's most affluent historic districts, celebrated for its architectural diversity, scenic views of the St. Johns River, and picturesque oak-lined streets. Built in 1948, this one-story residence features 3 bedrooms and 3 bathrooms, blending classic character with everyday functionality in a setting that continues to attract discerning buyers. Inside, the home showcases timeless hardwood flooring that adds warmth and character throughout. The kitchen is equipped with essential appliances including a dishwasher, electric range, microwave, and refrigerator, providing a practical layout for both daily living and entertaining. The interior offers comfortable living spaces with a layout that supports both privacy and flow, while the inclusion of an in-law suite presents added flexibility for guests, extended family, or potential rental income. The exterior features a fully fenced backyard, ideal for outdoor enjoyment, pets, or gardening. A rear patio creates a perfect space for relaxing or hosting gatherings, while the overall property maintains the charm expected in a historic Avondale home. The lot offers space to enjoy outdoor living while still being manageable, and the additional structure enhances the property's versatility. Conveniently positioned near Park Street, this home provides quick access to some of Jacksonville's most popular destinations. Nearby healthcare options include Ascension St. Vincent's Riverside, Baptist Medical Center Jacksonville, and UF Health Jacksonville. Shopping and dining are just minutes away at Shoppes of Avondale, Roosevelt Square, and Five Points, with several Florida State College at Jacksonville campuses also nearby. This home combines historic charm, practical features, and an unbeatable location in one of Jacksonville's most desirable neighborhoods. With its flexible living spaces, inviting outdoor areas, and proximity to everything Avondale has to offer, this property is ready for its next owner. Now available for showings, it presents an excellent opportunity to experience the lifestyle and convenience that make this area so special.

1316 Rensselaer Avenue, Jacksonville

Listing courtesy of MOMENTUM REALTY.

Selling Office: .

$1,874,000

5 Beds ⋅ 4 Baths ⋅ 2122052 MLS

Fully renovated 4-bedroom, 3.5-bathroom historic estate in Riverside, Jacksonville, Florida. This 3,964-square-foot residence sits on a corner lot with St. Johns River views and was completed after a 3.5-year renovation in 2025. The chef's kitchen features Wolf and Sub-Zero appliances and a custom white-and-brass range hood imported from Asia. Original inlaid wood flooring, 10-foot ceilings with gallery lighting, restored plaster walls, and original trim run throughout. The main home includes an original cast-iron tub on a riser. A 325-square-foot rear carriage house with full bathroom and original clawfoot tub provides flexible living space. One-car garage plus driveway parking for three vehicles. Unfinished basement for storage or future buildout. Near Memorial Park, the Cummer Museum, and downtown Jacksonville in the heart of Riverside. This historic Riverside estate in Jacksonville, Florida, delivers a rare combination of preserved architectural detail and modern luxury across 3,964 square feet. The 3.5-year renovation, completed in 2025, restored the home down to its bones while integrating premium modern systems and finishes throughout. The main level features original inlaid wood flooring that has been fully restored, 10-foot-plus ceilings fitted with gallery lighting, and original windows preserved throughout. Most interior walls are restored plaster, maintaining the texture and character of the original construction. Original trim has been beautifully refinished throughout the home. The chef's kitchen anchors the main level with Wolf and Sub-Zero appliances, including a Wolf range and Sub-Zero refrigeration. A custom white-and-brass range hood imported from Asia serves as the kitchen's centerpiece, blending artisan craftsmanship with modern function. The kitchen is designed for both daily use and entertaining. The primary bathroom in the main home features an original white cast-iron tub set on a riser. The home offers 4 bedrooms and 3.5 bathrooms total across the main residence and carriage house. The rear carriage house provides 325 square feet of flexible-use space with a full bathroom and an original blue painted cast-iron clawfoot tub -- a rare historic detail. This space can serve as a guest suite, home office, or studio. Exterior features include a large front porch with St. Johns River views, a rear deck, and restored exterior windows, trim, and stucco. The corner lot provides abundant parking for the area, including a one-car garage, driveway space for up to three additional vehicles, and street parking. An unfinished basement offers added storage capacity or future potential for additional finished space. Riverside is one of Jacksonville's most walkable neighborhoods, located near downtown Jacksonville and the St. Johns River. Dining within walking distance includes River and Post, Hoptinger, Josephine, The Brick, and 13 Gypsies. The Riverside Arts Market, Memorial Park, and the Cummer Museum of Art are all nearby. EverBank Stadium, home of the Jacksonville Jaguars, is a short drive away. This Riverside estate offers historic preservation and elevated modern living in one of Jacksonville, Florida's most sought-after neighborhoods.

1718 Osceola Street, Jacksonville

Listing courtesy of CHRISTIE'S INTERNATIONAL REAL ESTATE FIRST COAST.

$735,000

4 Beds ⋅ 3 Baths ⋅ 2121942 MLS

Timeless Avondale charm meets modern luxury in this beautifully reimagined 1924 cedar shake home. Featuring over $175,000 in curated updates, this residence preserves its original inlay wood floors while offering the conveniences today's buyers expect. Light-filled living spaces include a private downstairs suite with full bath and adjacent Florida room, ideal for guests, office, or multigenerational living. The kitchen opens to the dining area and features white cabinetry, quartz and walnut countertops, stainless appliances, gas range with pot filler, and a custom walnut pantry door. Upstairs, the redesigned primary suite offers a large custom closet and spa-like bath, plus two additional bedrooms and hall bath. Fenced backyard, garage with workshop, and restored greenhouse. Close to Avondale, Riverside, Murray Hill, and King Street.

1365 Belvedere Avenue, Jacksonville

Listing courtesy of ROUND TABLE REALTY.

Selling Office: .

$1,975,000

5 Beds ⋅ 7 Baths ⋅ 2117985 MLS

With Grand River views in the heart of Historic Avondale, this ''Prairie School'' influenced design was built in 1924 and enjoys a colorful past as the ''Bootlegger House''. A full renovation in 2015 is timeless with today's modern standards. A wide front veranda welcomes you to enter between twin copper lanterns and beveled glass entry. A grand entry foyer leads to spacious traditional Living and Dining rooms, plus sunlit side porch with river views. The kitchen is a cook's delight with newer stainless gas appliances, travertine counters, solid wood cabinetry and separate laundry with antique farm sink. Up the classic staircase are 4 large bedrooms and 3 full baths. The primary suite includes a sun/sitting room, private bath, walk-in closet and great river views.In the back yard is entertainment central with gas fire pit and summer kitchen grill. A separate building with it's own address features a studio and 2 car garage down and a full apartment up for Family or Air B&B

1880 Edgewood Avenue S, Jacksonville

Listing courtesy of CHRISTIE'S INTERNATIONAL REAL ESTATE FIRST COAST.

$4,250,000

7 Beds ⋅ 9 Baths ⋅ 2053150 MLS

This extremely rare gem in the heart of Historic Avondale, a neighborhood full of tree lined streets, local shops, restaurants, and parks all within walking distance, has hit the market! Renovated top to bottom, this estate spans almost 3/4 of an acre, with panoramic views of the St. John's River and downtown Jacksonville. The upstairs features 6 guest suites and a full guest house above the garage. Each room is expansive and airy, yet intimate and inviting. Natural light pours through each room and the expansive porch spans the entire length of the house allowing for all levels of entertaining. The location of this home is spectacular. Not only close to all the fun of Avondale, but also within 20-30 minutes of all major medical centers, the airport, and even the beaches! You must come see this remarkable home for yourself; words and photos truly can't capture it's greatness.

1875 Avondale Circle, Jacksonville

Listing courtesy of CHRISTIE'S INTERNATIONAL REAL ESTATE FIRST COAST.

Selling Office: .

$395,000

2 Beds ⋅ 2 Baths ⋅ 2052095 MLS

This FULLY REMODELED HOME w/ a separate GARAGE APARTMENT in RIVERSIDE is perfect for an owner who wants to generate additional income, investors looking for a turn-key investment, or a multi-generational family who just wants space! The main craftsman style home features 2 bedrooms, 1.5 baths, an open floor plan, CROWN MOLDING, & hardwood flooring. The open kitchen includes SHAKER CABINETS, granite countertops, stainless steel appliances, and white SUBWAY TILE backsplash. All bedrooms are large in size, & the inside laundry makes chores convenient. The garage apartment w/ 2 bedrooms & 1 bath is also renovated. With a full kitchen & laundry inside as well, this apartment is ready to AirBnb, host your guests or family, or rent out for a long-term lease. Ample parking in front of the 3-CAR GARAGE. ROOF - 2017, HVAC - 2017; Repiped - 2017; Rewired - 2018. Enjoy the charm of Riverside & its restaurants, bars, parks, & festivals while having easy access to I-10 & I-95. Don't miss this home!

2856 Rosselle Street, Jacksonville

Listing courtesy of KELLER WILLIAMS REALTY ATLANTIC PARTNERS.

Selling Office: .

$293,000

3 Beds ⋅ 2 Baths ⋅ 2041661 MLS

Mother-in-Law Suite/Bonus dwelling for possible rental income. Beautiful remodeled home with character kept in mind. Rare chance for additional living space so don't miss out! This property Features Refinished Original wood floors in main home, Remodeled Kitchen, Remodeled bathrooms, New appliances, New Hot water heaters, Crown molding, Large Wood Deck, New Electric Fireplace. Property also has a Large workshop/storage in rear. The additional living space is beautifully remodeled with tongue in groove ceiling, vinyl floors, wet bar and fridge! All this conveniently located in desirable Murray Hill area!

4832 Lawnview Street, Jacksonville

Listing courtesy of FLORIDA HOMES REALTY & MTG LLC.

Selling Office: .

$175,000

4 Beds ⋅ 3 Baths ⋅ 2041769 MLS

This unique ''fixer'' home is a great opportunity for investors seeking a rental property! It features an open floor plan, spacious front porch and a large, partially fenced-in yard. Additional highlights include A GUEST HOUSE WITH KITCHEN AND FULL BATH - live in the main house and rent the guest home! The AC is only a year old...and did I mention - NO HOA?! Don't miss this great home with so much potential! (Seller is wanting to sell as-is and this is reflected in the price.)

5127 Kingsbury Street, Jacksonville

Listing courtesy of UNITED REAL ESTATE GALLERY.

Selling Office: .

$340,000

6 Beds ⋅ 4 Baths ⋅ 2037435 MLS

Presenting a fantastic investment opportunity on the Westside of Jacksonville! This 4,525 sq ft triplex, built in 1953, sits on a spacious 0.412-acre lot. The property includes a main unit along with two attached apartments, one featuring one/one and the other is a 2/1 with a shower, and a compact kitchen. With great income potential, this property is ideal for investors looking to maximize their returns. Don't miss out on this rare find—schedule a viewing today and explore the possibilities!

5340 Kingsbury Street, Jacksonville

Listing courtesy of COLDWELL BANKER VANGUARD REALTY.

Selling Office: .

$485,000

5 Beds ⋅ 4 Baths ⋅ 2031001 MLS

Ask about lender incentives* This thoughtfully remodeled brick bungalow in an unbeatable location features two income-producing opportunities: one attached and one detached! Main home has 3/2 in the front + an attached 1/1 suite. With stunning hardwood & wood-look floors + natural light throughout, you'll find something to love in every room! The expansive living room w/recessed lighting & accent fireplace flows seamlessly into the formal dining for easy hosting. Updated kitchen boasts 42in cabinets w/built in-pantry and granite counters, plus a convenient side-entry door. All three bathrooms in the main home were remodeled w/stone counters, porcelain floors, tile-surround showers, steel tubs, and new vanities & lighting. The new primary en-suite also includes a walk-in closet and double vanity. Laundry is conveniently located in the hallway closet. The spacious attached suite is perfect for multi-gen living or STR, w/int & ext access, its own ductless AC, & room for a kitchenette. Relax or entertain on the covered front porch and back deck overlooking the blooming flower garden and yard. Large shed w/electric is workshop-ready, and the smaller shed has room for lawn equipment. The detached 578sf 1/1 is turnkey w/updated kitchen, wood-look floors, in-unit laundry, and perimeter drainage w/sump pump, as well as its own paver patio & shed. Each of the ADUs has its own assigned parking space in the extended driveway. Just one block from local eats & entertainment on Edgewood and a half mile to Four Corners and Murray Hill Park.

1020 Talbot Avenue, Jacksonville

Listing courtesy of ROOT REALTY LLC.

Selling Office: .

$425,000

4 Beds ⋅ 3 Baths ⋅ 2026978 MLS

Welcome to your dream home! Located in the coveted Avondale/Riverside area, this rare property is a true gem. The main home has original hard wood floors and features 3 bedrooms along with 2 full bathrooms, perfectly suited for family living. Additionally, there's a separate 2-story, 1 bed/1 bath apartment in the back, offering a versatile space for multi-generational living, a home business (perfect for Air BnB), or guest accommodations. Relax in your outdoor oasis complete with lush landscaping, new concrete patio for your outdoor gatherings plus a hot tub, providing you with the ultimate private retreat. This home also has updated windows, a new HVAC, updated electric panel and includes an RV hook up. Located outside of the Riverside Avondale Preservation (RAP) boundary line, offering all of the charm and allure of Avondale without the Historic District restrictions. This home combines classic appeal with modern amenities, perfect for Jacksonville living at its finest.

1521 Charon Road, Jacksonville

Listing courtesy of JPAR CITY AND BEACH.

Selling Office: .

$276,000

4 Beds ⋅ 2 Baths ⋅ 1222670 MLS

Just in time for summer! this newly renovated 4 bed 2 bath home boasts a very deep pool with a slide. excellent for multi generational living as the pool house doubles as an efficiency apart allowing for a separate private space for each generation of the house hold. Priced to move quick, come make an offer and be swimming by summer.

5417 Royce Avenue, Jacksonville

Listing courtesy of MOMENTUM REALTY.

Selling Office: .

$1,152,200

5 Beds ⋅ 4 Baths ⋅ 1236658 MLS

A stunning 1922 Mediterranean Revival style home located in the sought-after historic Avondale District. This stunning POOL home was showcased on both the 2007 & 2023 Riverside Avondale Preservation's annual Tour of Homes & is truly one of Avondale's finest homes! Features a gourmet kitchen, with separate bar area, that opens to a large family room with breakfast room, leading outside to the pool area. Home offers a spacious living room, separate dining room, downstairs library/office & charming, screened porch. Upstairs is the primary suite with fireplace, ensuite bathroom & large walk-in closet (was a former bedroom) 2 other bedrooms & bath, and a STUDIO/OFFICE. PLUS, there is a separate 1/1 apartment/guest suite with kitchenette, ATTACHED 2 car garage & basement! This one has it all!

1605 Avondale Avenue, Jacksonville

Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICES FLORIDA NETWORK REALTY.

Selling Office: .

$700,000

5 Beds ⋅ 4 Baths ⋅ 1242293 MLS

Stunning historic home with detached apartment on a double lot! This recently renovated exceptional property, located in beautiful, historic Avondale, seamlessly marries the charm of the past with modern comfort.. Main Residence - 4 Bedrooms, 2.5 Baths: The main residence includes 4 bedrooms and 2.5 baths and comprises the perfect blend of space, comfort, and character. High ceilings, hardwood floors, and large windows create a warm and inviting atmosphere throughout. The formal living room and cozy sunroom offer opportunities for relaxation and entertainment. The kitchen features modern appliances, ample counter space, and is open to the formal dining room. En suite guest room on the first floor with its own exterior access door. A half bath on the first floor is perfect for guests. Upstairs, three bedrooms and one bath. Use the whole floor as your private retreat! One BR fitted with custom closet fixtures was used as a walk-in closet/dressing room/lounging area. Detached Apartment - 1 Bedroom, 1 Bathroom, Laundry Hookups: The detached apartment is finished to the same exceptional standard as the main house. This space offers versatility to use as a guest suite, income-generating rental, or private retreat. With one bedroom, one bathroom, and convenient laundry hookups, this unit offers all the comforts of a modern home. Double Lot: This property is a true gem for outdoor enthusiasts and those who love to entertain. Sitting on a double lot, the fully fenced backyard is an oasis where you can create your own paradise. The options are endless, from gardening to hosting gatherings with friends and family. Enjoy the Florida sunshine under the shade of mature trees. And there is plenty of parking for the whole family plus guests! Current owners added French drains and irrigation system.

1330 Wolfe Street, Jacksonville

Listing courtesy of COWFORD REALTY & DESIGN LLC.

Selling Office: .

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